diff --git a/cli/bench/lsp_bench_standalone.rs b/cli/bench/lsp_bench_standalone.rs
index 68d2a0442b..0caa8620d4 100644
--- a/cli/bench/lsp_bench_standalone.rs
+++ b/cli/bench/lsp_bench_standalone.rs
@@ -36,6 +36,19 @@ fn incremental_change_wait(bench: &mut Bencher) {
       }),
     )
     .unwrap();
+
+  let (id, method, _): (u64, String, Option<Value>) =
+    client.read_request().unwrap();
+  assert_eq!(method, "workspace/configuration");
+  client
+    .write_response(
+      id,
+      json!({
+        "enable": true
+      }),
+    )
+    .unwrap();
+
   let (method, _maybe_diag): (String, Option<Value>) =
     client.read_notification().unwrap();
   assert_eq!(method, "textDocument/publishDiagnostics");
diff --git a/cli/lsp/diagnostics.rs b/cli/lsp/diagnostics.rs
index 8a3df34796..fb13f0257e 100644
--- a/cli/lsp/diagnostics.rs
+++ b/cli/lsp/diagnostics.rs
@@ -8,6 +8,7 @@ use super::documents;
 use super::documents::Document;
 use super::documents::Documents;
 use super::language_server;
+use super::language_server::StateSnapshot;
 use super::performance::Performance;
 use super::tsc;
 use super::tsc::TsServer;
@@ -36,6 +37,8 @@ use tokio::time::Duration;
 use tokio::time::Instant;
 use tokio_util::sync::CancellationToken;
 
+pub(crate) type SnapshotForDiagnostics =
+  (Arc<StateSnapshot>, Arc<ConfigSnapshot>, Option<LintConfig>);
 pub type DiagnosticRecord =
   (ModuleSpecifier, Option<i32>, Vec<lsp::Diagnostic>);
 pub type DiagnosticVec = Vec<DiagnosticRecord>;
@@ -91,10 +94,53 @@ impl DiagnosticsPublisher {
   }
 }
 
+#[derive(Clone, Default, Debug)]
+struct TsDiagnosticsStore(Arc<deno_core::parking_lot::Mutex<DiagnosticMap>>);
+
+impl TsDiagnosticsStore {
+  pub fn get(
+    &self,
+    specifier: &ModuleSpecifier,
+    document_version: Option<i32>,
+  ) -> Vec<lsp::Diagnostic> {
+    let ts_diagnostics = self.0.lock();
+    if let Some((diagnostics_doc_version, diagnostics)) =
+      ts_diagnostics.get(specifier)
+    {
+      // only get the diagnostics if they're up to date
+      if document_version == *diagnostics_doc_version {
+        return diagnostics.clone();
+      }
+    }
+    Vec::new()
+  }
+
+  pub fn invalidate(&self, specifiers: &[ModuleSpecifier]) {
+    let mut ts_diagnostics = self.0.lock();
+    for specifier in specifiers {
+      ts_diagnostics.remove(specifier);
+    }
+  }
+
+  pub fn invalidate_all(&self) {
+    self.0.lock().clear();
+  }
+
+  fn update(&self, diagnostics: &DiagnosticVec) {
+    let mut stored_ts_diagnostics = self.0.lock();
+    *stored_ts_diagnostics = diagnostics
+      .iter()
+      .map(|(specifier, version, diagnostics)| {
+        (specifier.clone(), (*version, diagnostics.clone()))
+      })
+      .collect();
+  }
+}
+
 #[derive(Debug)]
 pub(crate) struct DiagnosticsServer {
-  channel: Option<mpsc::UnboundedSender<()>>,
-  ts_diagnostics: Arc<Mutex<DiagnosticMap>>,
+  channel: Option<mpsc::UnboundedSender<SnapshotForDiagnostics>>,
+  ts_diagnostics: TsDiagnosticsStore,
   client: Client,
   performance: Arc<Performance>,
   ts_server: Arc<TsServer>,
@@ -115,44 +161,28 @@ impl DiagnosticsServer {
     }
   }
 
-  pub(crate) async fn get_ts_diagnostics(
+  pub(crate) fn get_ts_diagnostics(
     &self,
     specifier: &ModuleSpecifier,
     document_version: Option<i32>,
   ) -> Vec<lsp::Diagnostic> {
-    let ts_diagnostics = self.ts_diagnostics.lock().await;
-    if let Some((diagnostics_doc_version, diagnostics)) =
-      ts_diagnostics.get(specifier)
-    {
-      // only get the diagnostics if they're up to date
-      if document_version == *diagnostics_doc_version {
-        return diagnostics.clone();
-      }
-    }
-    Vec::new()
+    self.ts_diagnostics.get(specifier, document_version)
   }
 
-  pub(crate) async fn invalidate(&self, specifiers: Vec<ModuleSpecifier>) {
-    let mut ts_diagnostics = self.ts_diagnostics.lock().await;
-    for specifier in &specifiers {
-      ts_diagnostics.remove(specifier);
-    }
+  pub(crate) fn invalidate(&self, specifiers: &[ModuleSpecifier]) {
+    self.ts_diagnostics.invalidate(specifiers);
   }
 
-  pub(crate) async fn invalidate_all(&self) {
-    let mut ts_diagnostics = self.ts_diagnostics.lock().await;
-    ts_diagnostics.clear();
+  pub(crate) fn invalidate_all(&self) {
+    self.ts_diagnostics.invalidate_all();
   }
 
-  pub(crate) fn start(
-    &mut self,
-    language_server: Arc<Mutex<language_server::Inner>>,
-  ) {
-    let (tx, mut rx) = mpsc::unbounded_channel::<()>();
+  pub(crate) fn start(&mut self) {
+    let (tx, mut rx) = mpsc::unbounded_channel::<SnapshotForDiagnostics>();
     self.channel = Some(tx);
     let client = self.client.clone();
     let performance = self.performance.clone();
-    let stored_ts_diagnostics = self.ts_diagnostics.clone();
+    let ts_diagnostics_store = self.ts_diagnostics.clone();
     let ts_server = self.ts_server.clone();
 
     let _join_handle = thread::spawn(move || {
@@ -169,28 +199,19 @@ impl DiagnosticsServer {
           match rx.recv().await {
             // channel has closed
             None => break,
-            Some(()) => {
+            Some((snapshot, config, maybe_lint_config)) => {
               // cancel the previous run
               token.cancel();
               token = CancellationToken::new();
               diagnostics_publisher.clear().await;
 
-              let (snapshot, config, maybe_lint_config) = {
-                let language_server = language_server.lock().await;
-                (
-                  language_server.snapshot(),
-                  language_server.config.snapshot(),
-                  language_server.maybe_lint_config.clone(),
-                )
-              };
-
               let previous_ts_handle = ts_handle.take();
               ts_handle = Some(tokio::spawn({
                 let performance = performance.clone();
                 let diagnostics_publisher = diagnostics_publisher.clone();
                 let ts_server = ts_server.clone();
                 let token = token.clone();
-                let stored_ts_diagnostics = stored_ts_diagnostics.clone();
+                let ts_diagnostics_store = ts_diagnostics_store.clone();
                 let snapshot = snapshot.clone();
                 let config = config.clone();
                 async move {
@@ -226,17 +247,7 @@ impl DiagnosticsServer {
                   .unwrap_or_default();
 
                   if !token.is_cancelled() {
-                    {
-                      let mut stored_ts_diagnostics =
-                        stored_ts_diagnostics.lock().await;
-                      *stored_ts_diagnostics = diagnostics
-                        .iter()
-                        .map(|(specifier, version, diagnostics)| {
-                          (specifier.clone(), (*version, diagnostics.clone()))
-                        })
-                        .collect();
-                    }
-
+                    ts_diagnostics_store.update(&diagnostics);
                     diagnostics_publisher.publish(diagnostics, &token).await;
 
                     if !token.is_cancelled() {
@@ -309,9 +320,15 @@ impl DiagnosticsServer {
     });
   }
 
-  pub(crate) fn update(&self) -> Result<(), AnyError> {
+  pub(crate) fn update(
+    &self,
+    message: SnapshotForDiagnostics,
+  ) -> Result<(), AnyError> {
+    // todo(dsherret): instead of queuing up messages, it would be better to
+    // instead only store the latest message (ex. maybe using a
+    // tokio::sync::watch::channel)
     if let Some(tx) = &self.channel {
-      tx.send(()).map_err(|err| err.into())
+      tx.send(message).map_err(|err| err.into())
     } else {
       Err(anyhow!("diagnostics server not started"))
     }
diff --git a/cli/lsp/language_server.rs b/cli/lsp/language_server.rs
index 928a427fc7..af6bcf9947 100644
--- a/cli/lsp/language_server.rs
+++ b/cli/lsp/language_server.rs
@@ -40,6 +40,7 @@ use super::diagnostics::DiagnosticsServer;
 use super::documents::to_hover_text;
 use super::documents::to_lsp_range;
 use super::documents::AssetOrDocument;
+use super::documents::Document;
 use super::documents::Documents;
 use super::documents::LanguageId;
 use super::logging::lsp_log;
@@ -754,15 +755,8 @@ impl Inner {
     &mut self,
     specifier: &ModuleSpecifier,
     params: DidOpenTextDocumentParams,
-  ) {
+  ) -> Document {
     let mark = self.performance.mark("did_open", Some(&params));
-
-    if params.text_document.uri.scheme() == "deno" {
-      // we can ignore virtual text documents opening, as they don't need to
-      // be tracked in memory, as they are static assets that won't change
-      // already managed by the language service
-      return;
-    }
     let language_id =
       params
         .text_document
@@ -786,17 +780,8 @@ impl Inner {
       content,
     );
 
-    if document.is_diagnosable() {
-      self
-        .diagnostics_server
-        .invalidate(self.documents.dependents(specifier))
-        .await;
-      if let Err(err) = self.diagnostics_server.update() {
-        error!("{}", err);
-      }
-    }
-
     self.performance.measure(mark);
+    document
   }
 
   async fn did_change(&mut self, params: DidChangeTextDocumentParams) {
@@ -811,11 +796,8 @@ impl Inner {
         if document.is_diagnosable() {
           self
             .diagnostics_server
-            .invalidate(self.documents.dependents(&specifier))
-            .await;
-          if let Err(err) = self.diagnostics_server.update() {
-            error!("{}", err);
-          }
+            .invalidate(&self.documents.dependents(&specifier));
+          self.send_diagnostics_update();
         }
       }
       Err(err) => error!("{}", err),
@@ -839,10 +821,8 @@ impl Inner {
     if self.is_diagnosable(&specifier) {
       let mut specifiers = self.documents.dependents(&specifier);
       specifiers.push(specifier.clone());
-      self.diagnostics_server.invalidate(specifiers).await;
-      if let Err(err) = self.diagnostics_server.update() {
-        error!("{}", err);
-      }
+      self.diagnostics_server.invalidate(&specifiers);
+      self.send_diagnostics_update();
     }
     self.performance.measure(mark);
   }
@@ -886,13 +866,13 @@ impl Inner {
     if let Err(err) = self.update_tsconfig().await {
       self.client.show_message(MessageType::WARNING, err).await;
     }
-    if let Err(err) = self.diagnostics_server.update() {
-      error!("{}", err);
-    }
+
     self.documents.update_config(
       self.maybe_import_map.clone(),
       self.maybe_config_file.as_ref(),
     );
+
+    self.send_diagnostics_update();
   }
 
   async fn did_change_watched_files(
@@ -935,10 +915,8 @@ impl Inner {
         self.maybe_import_map.clone(),
         self.maybe_config_file.as_ref(),
       );
-      self.diagnostics_server.invalidate_all().await;
-      if let Err(err) = self.diagnostics_server.update() {
-        error!("Cannot update diagnostics: {}", err);
-      }
+      self.diagnostics_server.invalidate_all();
+      self.send_diagnostics_update();
     }
     self.performance.measure(mark);
   }
@@ -1180,8 +1158,7 @@ impl Inner {
       let mut code_actions = CodeActionCollection::default();
       let file_diagnostics = self
         .diagnostics_server
-        .get_ts_diagnostics(&specifier, asset_or_doc.document_lsp_version())
-        .await;
+        .get_ts_diagnostics(&specifier, asset_or_doc.document_lsp_version());
       for diagnostic in &fixable_diagnostics {
         match diagnostic.source.as_deref() {
           Some("deno-ts") => {
@@ -2337,6 +2314,17 @@ impl Inner {
     self.performance.measure(mark);
     Ok(maybe_symbol_information)
   }
+
+  fn send_diagnostics_update(&self) {
+    let snapshot = (
+      self.snapshot(),
+      self.config.snapshot(),
+      self.maybe_lint_config.clone(),
+    );
+    if let Err(err) = self.diagnostics_server.update(snapshot) {
+      error!("Cannot update diagnostics: {}", err);
+    }
+  }
 }
 
 #[lspower::async_trait]
@@ -2346,7 +2334,7 @@ impl lspower::LanguageServer for LanguageServer {
     params: InitializeParams,
   ) -> LspResult<InitializeResult> {
     let mut language_server = self.0.lock().await;
-    language_server.diagnostics_server.start(self.0.clone());
+    language_server.diagnostics_server.start();
     language_server.initialize(params).await
   }
 
@@ -2359,14 +2347,29 @@ impl lspower::LanguageServer for LanguageServer {
   }
 
   async fn did_open(&self, params: DidOpenTextDocumentParams) {
+    if params.text_document.uri.scheme() == "deno" {
+      // we can ignore virtual text documents opening, as they don't need to
+      // be tracked in memory, as they are static assets that won't change
+      // already managed by the language service
+      return;
+    }
+
     let (client, uri, specifier, had_specifier_settings) = {
       let mut inner = self.0.lock().await;
       let client = inner.client.clone();
       let uri = params.text_document.uri.clone();
       let specifier = inner.url_map.normalize_url(&uri);
-      inner.did_open(&specifier, params).await;
+      let document = inner.did_open(&specifier, params).await;
       let has_specifier_settings =
         inner.config.has_specifier_settings(&specifier);
+      if document.is_diagnosable() {
+        let specifiers = inner.documents.dependents(&specifier);
+        inner.diagnostics_server.invalidate(&specifiers);
+        // don't send diagnotics yet if we don't have the specifier settings
+        if has_specifier_settings {
+          inner.send_diagnostics_update();
+        }
+      }
       (client, uri, specifier, has_specifier_settings)
     };
 
@@ -2376,12 +2379,12 @@ impl lspower::LanguageServer for LanguageServer {
       let language_server = self.clone();
       tokio::spawn(async move {
         let response = client.specifier_configuration(&uri).await;
+        let mut inner = language_server.0.lock().await;
         match response {
           Ok(specifier_settings) => {
-            // now update the config
-            let mut inner = language_server.0.lock().await;
+            // now update the config and send a diagnostics update
             inner.config.set_specifier_settings(
-              specifier,
+              specifier.clone(),
               uri,
               specifier_settings,
             );
@@ -2390,6 +2393,14 @@ impl lspower::LanguageServer for LanguageServer {
             error!("{}", err);
           }
         }
+        if inner
+          .documents
+          .get(&specifier)
+          .map(|d| d.is_diagnosable())
+          .unwrap_or(false)
+        {
+          inner.send_diagnostics_update();
+        }
       });
     }
   }
@@ -2712,12 +2723,9 @@ impl Inner {
 
     // now that we have dependencies loaded, we need to re-analyze them and
     // invalidate some diagnostics
-    self.diagnostics_server.invalidate(vec![referrer]).await;
+    self.diagnostics_server.invalidate(&[referrer]);
+    self.send_diagnostics_update();
 
-    self.diagnostics_server.update().map_err(|err| {
-      error!("{}", err);
-      LspError::internal_error()
-    })?;
     self.performance.measure(mark);
     Ok(Some(json!(true)))
   }
diff --git a/cli/tests/integration/lsp_tests.rs b/cli/tests/integration/lsp_tests.rs
index 12c50e757e..f0e6faa6ba 100644
--- a/cli/tests/integration/lsp_tests.rs
+++ b/cli/tests/integration/lsp_tests.rs
@@ -57,6 +57,11 @@ where
     .write_notification("textDocument/didOpen", params)
     .unwrap();
 
+  handle_configuration_request(client);
+  read_diagnostics(client).0
+}
+
+fn handle_configuration_request(client: &mut LspClient) {
   let (id, method, _) = client.read_request::<Value>().unwrap();
   assert_eq!(method, "workspace/configuration");
   client
@@ -70,8 +75,6 @@ where
       }]),
     )
     .unwrap();
-
-  read_diagnostics(client).0
 }
 
 fn read_diagnostics(client: &mut LspClient) -> CollectedDiagnostics {
@@ -490,6 +493,7 @@ fn lsp_import_assertions() {
       }),
     )
     .unwrap();
+  handle_configuration_request(&mut client);
 
   let diagnostics = CollectedDiagnostics(did_open(
     &mut client,
diff --git a/test_util/src/lsp.rs b/test_util/src/lsp.rs
index 92dc98102c..948dc4da64 100644
--- a/test_util/src/lsp.rs
+++ b/test_util/src/lsp.rs
@@ -122,7 +122,16 @@ where
   R: de::DeserializeOwned,
 {
   let maybe_params = match maybe_params {
-    Some(params) => Some(serde_json::from_value(params)?),
+    Some(params) => {
+      Some(serde_json::from_value(params.clone()).map_err(|err| {
+        anyhow::anyhow!(
+          "Could not deserialize message '{}': {}\n\n{:?}",
+          method,
+          err,
+          params
+        )
+      })?)
+    }
     None => None,
   };
   Ok((method, maybe_params))